Lithium hydroxide, monohydrate → 3-Bromo-5-[(dipropylamino)carbonyl]Benzoic Acid

HRID 1350922Notes

Reaction equation

HRID 1350922 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[O:13])[CH:11]=1)[C:5]([O:7]C)=[O:6].O.[OH-].[Li+]>C1COCC1.O.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[O:13])[CH:11]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21939662Methyl 3-bromo-5-(dipropylcarbamoyl)benzoate

Product 1

HCID 112903703-Bromo-5-[(dipropylamino)carbonyl]Benzoic Acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (XXI, PREPARATION 3, 1.4 g, 4.1 mmol) in THF/water/methanol (4/2/2, 8 mL) is added to lithium hydroxide monohydrate (0.17 g, 4.05 mmol). The mixture is stirred at 20 degrees −25 degrees C. for 1 hour and then solvent is removed under reduced pressure. The residue is dissolved in water (50 mL) and hydrochloric acid (1 N) is added to adjust the pH to about 3. The aqueous mixture is extracted with ethyl acetate and the organic phase is separated and dried over magnesium sulfate to give the title compound. Analytical calculated for C14H18BrNO3: C, 51.23;H, 5.53; N, 4.27; Br, 24.35. Found: C, 51.37;H, 5.56; N, 4.28.

Workup

  1. customsolvent is removed under reduced pressure
  2. dissolutionThe residue is dissolved in water (50 mL)
  3. additionhydrochloric acid (1 N) is added
  4. extractionThe aqueous mixture is extracted with ethyl acetate
  5. customthe organic phase is separated
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-fb29d1ecd9de4bc8ab0104ed5f610a4e
Source dataset
uspto-grants-2007_05
Patent number
US07214715B2

Reaction notes

Loading…